“From Kenosha’s streetcar to Delavan’s Andes Candies… and through the heart of Lake Geneva”
Quickie Summary: Short as it is, State “Trunk” Highway 50 is a major east-west thoroughfare connecting Kenosha with Delavan and moving a lot of traffic throughout the region. Along with its endpoints, places like Bristol, Paddock Lake, Pleasant Prairie, and especially Lake Geneva are served by Highway 50 as it muscles its way across the eastern half of southern Wisconsin. Much of the route is expressway-like and provides good connections to other major routes.
Wisconsin Highway 50 Road Trip
The Drive (East To West):
Kenosha
Highway 50 begins within a few blocks of Lake Michigan in downtown Kenosha (pop. 99,889), Wisconsin’s fourth largest city. Originally known as Pike and then Southport (a name many businesses still use), Kenosha got its current name in 1850, a descendant name from the original Potawatomi name, Mas-ke-no-zha, meaning “place of the Pike.”
Today, Kenosha just keeps changing. Relying on heavy manufacturing for many, many years, the demise of the American auto industry in the 1970s and 80s took a heavy toll. Kenosha’s economy today hums along, however, buoyed by services and health care. Some manufacturing remains and the area contains headquarters for companies like Jockey International and Snap-On Tools. Proximity to Chicago and Milwaukee make it a handy area for transportation, warehousing and tourism. A recent influx of Chicago-area residents heightens the Packers-Bears tension every autumn. Kenosha actually did have its own NFL team once: the Kenosha Maroons, which played for one season in 1924, posting no wins.
Kenosha – Downtown & HarborPark
Highway 50 begins as 63rd Street at Sheridan Road (Highway 32), just south of Kenosha’s downtown and HarborPark. Formerly the site of a massive American Motors assembly plant that sat right along the lake, HarborPark is now an upscale-leaning area giving rise to lakefront condos, museums, and emerging small businesses with a streetcar system with a trolley connecting them all.
HarborPark is basically the eastern and northern edge of Kenosha’s downtown; attractions there include the Kenosha Public Museum and the Museum of the Civil War. Two new microbreweries have opened up within blocks of each other, Rustic Road Brewing Company on 6th Avenue and Public Craft Brewing Company on 58th Street. Adjacent to Public Craft you’ll find Frank’s Diner, a classic diner located in a real train car that’s been whipping up classic breakfasts for hungry locals since 1926, when a team of horses towed the train car to its present location. Plenty of tourists check out Frank’s too, as it’s been featured in numerous travel magazines, on Food Network’s Diners, Drive-Ins, and Dives, and now – I’m sure this makes them proudest – as part of the State Trunk Tour.
Kenosha’s manufacturing history is massive: not only were cars produced here, but Simmons made bedding, mattresses, and even wooden insulators and cheese boxes here; they moved their headquarters to Atlanta in 1975. The G. Leblanc Corporation was the nation’s largest manufacturer of wind instruments here for over half a century. Snap-On still builds tools in Kenosha and Ocean Spray turns cranberries into juices at a major facility. Jockey was founded in Kenosha in 1876, invented men’s “Y”-front briefs in 1934, and still has its headquarters in the city. Many other smaller machine shops continue to operate and supply manufacturers around the nation. To show how the economy has changed, Abbott Labs is now the largest employer in the Kenosha area.
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| Car manufacturing in Kenosha dates back to 1902, when Thomas Jeffery switched from making bicycles to building cars. Since then, models by American Motors, Chrysler, Dodge, Nash, and Renault have been made here. Full production stopped in 1987, although component-making continues. |
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Simmons Island lies north of Kenosha’s harbor and downtown district, right along the lake (of course.) The Simmons Island Lighthouse (left) was built of Cream City brick in 1886 and has marked the harbor entrance ever since. Dormant for 90 years, the lighthouse was reactivated in 1996. |
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A remnant once of once-mighty American Motors Lakefront Plant sits amidst parkland and boats bobbing in the Kenosha marina in HarborPark – a reminder of what once stood here. |
| Kenosha’s streetcar loop runs two miles through HarborPark and around the downtown, connecting to the METRA station and museum attractions. After touring around on the streetcar, you can pick up the beginning of Highway 50 a few blocks south of here. |  |
Have you checked out enough of Kenosha’s downtown and HarborPark sights? Then let’s get to the start of Highway 50 and get moving west!
Highway 50 begins as 63rd Street at Highway 32 (Sheridan Road, intersection pictured above), a rather unassuming start to a road that becomes a major artery across the southern part of the state. Except for a small jog in town here (Highway 50 used to end at 75th Street, about a mile further south), the route has remained essentially unchanged since state highways were first laid out in 1918.
DRIVE-IN ALERTS!! Heading west from downtown, Highway 50 continues on 63rd Street before angling southwest on Roosevelt Road. Several older restaurants and drive-ins dot this area, including Andy’s Drive In (at 30th Avenue & Highway 50, 262-658-2067), featuring “Classic Car Nights” with street rods and cars from the ’50s and ’60s every Wednesday evening from May through October.
Another noteworthy drive-in diversion is The Spot, which requires a jog south to 75th Street along 22nd Avenue (75th used to be Highway 50 all the way to the lake). The Spot serves up incredibly tasty burgers, fries, deep fried cheese curds, root beer floats, malts, ice cream and more. After all, one can’t drive on an empty stomach. To re-join Highway 50, head west on 75th Street; at 39th Avenue, Highway 50 joins 75th Street again.
Heading out of Kenosha, Highway 50 is clearly the area’s main commercial thoroughfare; if you need something, you’ll find it along this stretch. As you reach the intersection with Highway 31, you reach Pleasant Prairie (pop. 19,719 and rapidly counting), the booming village whose large tracts of available land are quickly filling up with subdivisions, shopping centers and new manufacturing plants. You can look south as you drive past County Highway H and see the billowing steam from the local power plant, which is often visible from an airplane 100 miles away.
With all the new stuff popping up, it’s only fitting to note the history, too. Just west of Highway 31, you’ll go up over two sets of railroad tracks; in between, an exit ramp for “77th Avenue”, which leads to some businesses in what looks like a remnant of a town in itself. It is: it’s called Truesdell. The settlement, located along the main rail line between Milwaukee and Chicago, was a switching point for trains and hosted passenger trains until 1945. Truesdell’s post office opened in 1870 and lasted until 1953, when Kenosha overtook the town. Their postmistress, Jennie Alsted, operated the post office from her home’s back porch for the final 31 years of its existence.
Highway 50 is a busy 4-lane thoroughfare here, and a few more miles west you reach the intersection with I-41/94. Massive developments now sit at an interchange that once housed nothing but a Howard Johnson’s restaurant and motel, one gas station and a McDonald’s. Today, the only White Castle in Wisconsin is on Highway 50 just east of I-94 – check out the drive-thru lines at 2am.
*** BREWERY & BRATS ALERT ***
Additional State Trunk Tour-approved Pit Stops. For beer and bar food lovers, there are two key pit stops in the vicinity of Highway 50’s interchange with I-94/41: the R’Noggin Brewing Company, and the Brat Stop. The R’Noggin Brewing Company is about 1/2 mile north of Highway 50 along the east side Frontage Road with I-41/94. Launched in 2016 by two brothers inside a former D.O.T. truck service building, R’Noggin offers a variety of craft brews including many seasonals. Their Tap Room is open seven days a week and includes outdoor seating via the wide-open garage doors – ones that once served huge trucks – and allowing for outdoor imbibing.
A longer tradition awaits at the Brat Stop, a local hangout since 1961. With an extensive bar, restaurant, cheese soup, live music stage, event venue space and more, the Brat Stop sells a ton of brats every week – literally. It’s also the first place State Trunk Tour author’s father, who grew up in Kenosha, got busted for trying to use a fake ID. And that was back the year it opened! Expect to see a lot of Illinois license plates in the lot and plenty of Bears, Cubs, and White Sox fans showing up to watch games, but hey – don’t let that stop you from going in.
Further west on Highway 50, you can move at a pretty good clip. The intersection with U.S. Highway 45 can take you south less than one mile to Bristol, home of Merkt’s Cheese Company (262-857-2316) and those delicious spreads. Stop into their store and pick up the Sharp Cheddar with Wine or some other variation, and don’t forget the crackers. Cheese spread is kind of messy without crackers.
Further west sits Paddock Lake (pop 3,200). Highway 50 runs right through town; it’s the only place between I-94 and Lake Geneva where the speed limit isn’t 55. It’s 35, and I’m guessing speeding tickets are a handy source of income for the town, so watch your speed!
Brass Ball Corners.
On the west side of Paddock Lake, where Highway 83 comes in from the south and Highway 75 leads north, is a little intersection known as Brass Ball Corners. This dates back to the 1840s, when today’s Highway 50 was part of a busy trade route and trail connecting Kenosha, Lake Geneva, and Janesville. A farmer named Seth Huntoon realized this junction would make a popular place for travelers to stop and rest. He built an inn and, to help draw attention to it, hung a wooden ball gilded in gold at the intersection. People decided it looked more like brass, and ever since it’s been known as “Brass Ball Corners”. A more detailed story is here. No word on how many “brass balls” jokes have been made during this 170-year-run.
Bait stores abound in case you want to fish on Paddock Lake or Hooker Lake (insert snickering here.) Highway 83, just in from Illinois, joins 50 for a short stretch while the brief Highway 75 heads north to access the Bong Recreation Area (insert more snickering here). Highway 83 joins 50 for about 5-6 miles before it heads northwest to Burlington.
Continuing west on Highway 50 brings you to just one of Wisconsin’s tourist meccas, Lake Geneva. As you approach the U.S. 12 Freeway, gaze at the Grand Geneva Resort to your right. Or better yet, pull onto the access road and check it out. It was originally a Playboy Club & Resort. Hugh Hefner’s Playboy empire began in Chicago, and since the law states Chicagoans must vacation in Lake Geneva, ol’ Hef built a Playboy Club here. It closed in 1987 but the impressiveness of today’s Grand Geneva will make you forget all about bunny tails. The Grand Geneva Resort & Spa is a sprawling complex featuring world-class golf, spas, event hosting and more… it even has its own small airport. The drive in off Highway 50 twists and turns for what seems like a mile or two before you reach The Lodge and other resort buildings. It’s a world away from the hustle and bustle of Milwaukee and Chicago, as well as the bustle of towns brimming with tourists. This is a “get away from it all” resort and spa.
Lake Geneva
Just on the other side of U.S. 12 is Lake Geneva (pop. 7,872) itself. A longtime popular vacation town, Lake Geneva’s downtown strip is filled with stores, restaurants and attractions that cater to the thousands upon thousands of tourists – many from Illinois – who descend on the city every year. On warm weather days, it can be a slow push through towhttp://www.lakegenevawi.com/n, but the activity can grab your attention and you’ll enjoy the views. Because of its resort-like nature, many refer to Lake Geneva as the “Newport of the West.”
On summer weekends, expect a packed Highway 50 as it goes through the heart of Lake Geneva filled with tourists and sightseers ready for a great day in this vacation town. The ratio of Illinois plates is rather high here.
Lake Geneva is the city; Geneva Lake is the lake. Filled with boats in the summer, the lake is the second deepest in the state and measures 21 miles around its shoreline. Mansions, including those occupied by the Wrigley family of chewing gum and Chicago Cubs fame, line the shore, especially between Lake Geneva and Williams Bay. Many residents along the shore actually get their mail via boat. Lake Geneva brings out the creator in people: it was home to Sidney Smith, creator of the Andy Gump comic strip; Joe and Jay Martin, writers of the Mr. Boffo, Willy ‘N Ethel, and Tommy comics; and this is the place where the Dungeons & Dragons role-playing game was developed. A soap opera was created here too, as evidenced by the convenient State Trunk Tour Tidbit below.
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| The Young and the Restless soap opera was developed by producers William Bell and Lee Phillips in Lake Geneva. They set the show in nearby Genoa City, although they modeled the town after Lake Geneva… the two towns are actually quite different. |
Golf, anyone? Lake Geneva features championship courses at places like Geneva National, right along Highway 50 about four miles west of Lake Geneva. Geneva National features courses designed by Arnold Palmer and Lee Trevino and is rated in Wisconsin’s top 10 by Golf Digest, a hefty feat in a state with so many great courses.
Lake Geneva embraces winter, too. The U.S. National Snow Sculpting Championships take place here the first weekend in February and carvers from all over the nation create some amazing designs. Too bad they all eventually melt – even though with Wisconsin winters, some last for quite a while!
After crossing a busy 4-way stop intersection with Highway 67, Highway 50 heads toward Delavan Lake, immensely popular with fishing enthusiasts. It’s possible – though unlikely – that one could snag the elephant buried in the lake. Yes, the elephant. We know nothing further on this at this time, but we’ll delve into it further next time we’re at a bar there…
Delavan
After ducking past some new development and under I-43, Highway 50 enters Delavan (pop. 7,956) and ends at Highway 11, just short of downtown. Delavan is quite the circus town: it’s the original home of P.T. Barnum’s “Greatest Show On Earth” (P.T. stood for Phineas Taylor, in case you were curious) and from 1847-1895 about 26 circuses made their headquarters here. A 12-year-old runaway named Harry Houdini stayed in a livery stable in Delavan’s Park Hotel, along Highway 11 on the west side of town. Delavan is the native home of Gary Berghoff (Radar O’Reilly on M*A*S*H) and home to those delicious Andes Candies. Also on the west side of Delavan lies the site for Wisconsin’s first School for the Deaf.
Highway 50 is a major east-west highway in southeastern Wisconsin. It’s a city street, a tourist-packed main street and a four-lane expressway, giving access to everything from Lake Michigan to tiny fishing ponds, new museums and old historical spots, championship golf courses and sprawling resorts.. all within 45 miles. It makes for a great, variety-packed short afternoon trip.
From Delavan, Highway 11 brings you back east, towards Elkhorn, Burlington, and Racine; west is Janesville, Monroe, and points beyond!
CONNECTIONS:
East Terminus:
Can connect immediately to: Highway 32
Can connect nearby to: Highway 158, about 1 mile north; Highway 31, about 5 miles west; I-94/41, about 8 miles west
West Terminus:
Can connect immediately to: Highway 11
Can connect nearby to: I-43, about one mile east; Highway 67, about 8 miles east
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